Synthesis of multisubstituted quinolines from Baylis-Hillman adducts obtained from substituted 2-chloronicotinaldehydes and their antimicrobial activity

Bioorganic and Medicinal Chemistry

Volumn 14, Issue 13, 2006, Pages 4600-4609

  Narender, P ^a   Srinivas, U ^a   Ravinder, M ^a   Ananda Rao, B ^a   Ramesh, Ch ^a   Harakishore, K ^a   Gangadasu, B ^a   Murthy, U S N ^a   Jayathirtha Rao, V ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Antimicrobial evaluation; Baylis Hillman adducts; Multisubstituted quinolines; SN2 SNAr elimination reaction; Substituted 2 chloronicotinaldehydes

Indexed keywords

2 CHLORONICOTINALDEHYDE DERIVATIVE; 3 (2 CHLORO 5 METHYL 3 PYRIDYL) 2 (2 NITROPROPYL) 2 PROPENOATE; 3 ETHYL 6 METHYL 2 PHENYL 8 METHYL 3,6 QUINOLINECARBOXYLATE; 3 PHENYL 9 METHYL 7,8 DIHYDRO 6H CYCLOPENTA[G]QUINOLIN 6 ONE; 3,9 DIMETHYL 7,8 DIHYDRO 6H CYCLOPENTA[G]QUINOLIN 6 ONE; 6 ETHYL 2 METHYL 8 METHYL 2,6 QUINOLINEDICARBOXYLATE; ACETIC ACID DERIVATIVE; ALDEHYDE DERIVATIVE; CYCLOPENTA[G]QUINOLINE DERIVATIVE; DIMETHYL 8 METHYL 2,6 QUINOLINECARBOXYLATE; ETHANE; ETHYL 2 [(2 CHLORO 5 METHYL 6 PHENYLPYRIDINE 3 YL) (HYDROXY)METHYL]ACRYLATE; ETHYL 2 [(2 CHLORO 5 METHYLPYRIDINE 3 YL) (HYDROXY)METHYL]ACRYLATE; ETHYL 2 [(2 CHLORO 5 PHENYLPYRIDINE 3 YL) (HYDROXY)METHYL]ACRYLATE; ETHYL 2 PHENYL 3 METHYL 8 CYANO 6 QUINOLINECARBOXYLATE; ETHYL 2 PHENYL 3,8 DIMETHYL 6 QUINOLINECARBOXYLATE; ETHYL 3 PHENYL 8 CYANO 6 QUINOLINECARBOXYLATE; ETHYL 3 PHENYL 8 METHYL 6 QUINOLINECARBOXYLATE; ETHYL 3,8 DIMETHYL 6 QUINOLINECARBOXYLATE; ETHYL 6 CHLORO 5 [1 HYDROXY 2 (METHOXYCARBONYL)) 2 PHENYL NICOTINATE; ETHYLCYANOACETATE; METHYL 2 [(2 CHLORO 5 METHYLPYRIDINE 3 YL) (HYDROXY)METHYL]ACRYLATE; METHYL 2 [[(2 CHLORO 5 (4 METHOXYPHENYL)PYRIDINE 3 YL)] (HYDROXY)METHYL]ACRYLATE; METHYL 3 (4 METHOXYPHENYL) 8 METHYL 6 QUINOLINECARBOXYLATE; METHYL 3 METHYL 8 CYANO 6 QUINOLINECARBOXYLATE; METHYL 3,8 DIMETHYL 6 QUINOLINECARBOXYLATE; METHYL 6 CHLORO 5 [1 HYDROXY 2 (METHOXYCARBONYL)PROP 2 EN 1 YL]PYRIDINE 2 CARBOXYLATE; NITROETHANE; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG; 3-PYRIDINALDEHYDE; ALDEHYDE; ANTIFUNGAL AGENT; ANTIINFECTIVE AGENT; NICOTINALDEHYDE;

ADDUCTION; ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ANTIMICROBIAL ACTIVITY; ARTICLE; BAYLIS HILLMAN REACTION; CONTROLLED STUDY; DRUG SYNTHESIS; ELIMINATION REACTION; NONHUMAN; BACTERIUM; CHEMISTRY; DRUG EFFECT; FUNGUS; SYNTHESIS;

ACETATES; ALDEHYDES; ANTI-BACTERIAL AGENTS; ANTIFUNGAL AGENTS; BACTERIA; FUNGI; QUINOLINES;

EID: 33746533902     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2006.02.020     Document Type: Article

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77. 2 for 20 min. Agar cup bioassay was employed for testing antifungal activity. The medium was poured into sterile Petri dishes under aseptic conditions in a laminar flow chamber. When the medium in the plates solidified, 0.5 mL of (week old) culture of test organism was inoculated and uniformly spread over the agar surface with a sterile L-shaped rod. Solutions were prepared by dissolving the compound in DMSO and different concentrations were made (30 and 100 μg/mL). After inoculation, cups were scooped out with 6 mm sterile cork borer and the lids of the dishes were replaced. To each cup different concentrations of test solutions (30,100 μg/mL) were added. Controls were maintained with acetone and Clotrimazole (100 μg/mL). The treated and the controls were kept at room temperature for 48 h. Inhibition zones were measured and the diameter was calculated in millimeter. Three to four replicates were maintained for each treatment. Media. Potato Dextrose broth and Potato Dextrose agar were procured from M/S Himedia Laboratories, Mumbai.